Sophoraflavanone_G (BioDeep_00000230183)

Main id: BioDeep_00000012050

 

PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(2,4-dihydroxyphenyl)-8-(5-methyl-2-(1-methylethenyl)-4-hexenyl)-, (S-(R*,S*))-

化学式: C25H28O6 (424.1885788)
中文名称: 槐黄烷酮 G, 苦参酚 F, 苦参总黄酮, 苦参醇 F, 苦参醇F
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=CCC(CC1=C2C(=C(C=C1O)O)C(=O)CC(O2)C3=C(C=C(C=C3)O)O)C(=C)C)C
InChI: InChI=1S/C25H28O6/c1-13(2)5-6-15(14(3)4)9-18-20(28)11-21(29)24-22(30)12-23(31-25(18)24)17-8-7-16(26)10-19(17)27/h5,7-8,10-11,15,23,26-29H,3,6,9,12H2,1-2,4H3/t15-,23+/m1/s1

描述信息

Sophoraflavanone G is a tetrahydroxyflavanone having a structure of naringenin bearing an additional hydroxyl substituent at position 2 as well as a (2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl (lavandulyl) substituent at position 8. It has a role as an antioxidant, an antimalarial, an antimicrobial agent and a plant metabolite. It is a tetrahydroxyflavanone, a member of 4-hydroxyflavanones and a (2S)-flavan-4-one. It is functionally related to a (S)-naringenin.
Sophoraflavanone G is a natural product found in Sophora stenophylla, Sophora moorcroftiana, and other organisms with data available.
A tetrahydroxyflavanone having a structure of naringenin bearing an additional hydroxyl substituent at position 2 as well as a (2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl (lavandulyl) substituent at position 8.
Sophoraflavanone G (Kushenol F) is iaolated from Sophora flavescens and shows anti-tumor and anti-inflammatory properties.? Sophoraflavanone G (Kushenol F) induces MDA-MB-231 and HL-60 cells apoptosis through suppression of MAPK-related pathways[1][2].
Sophoraflavanone G (Kushenol F) is iaolated from Sophora flavescens and shows anti-tumor and anti-inflammatory properties.? Sophoraflavanone G (Kushenol F) induces MDA-MB-231 and HL-60 cells apoptosis through suppression of MAPK-related pathways[1][2].

同义名列表

15 个代谢物同义名

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(2,4-dihydroxyphenyl)-8-(5-methyl-2-(1-methylethenyl)-4-hexenyl)-, (S-(R*,S*))-; (2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-4H-chromen-4-one; (2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2R)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one; (S)-2-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-8-((R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl)chroman-4-one; (2S)-5,7,2,4-tetrahydroxy-8-lavandulylflavanone; 5,7,2,4-tetrahydroxy-8-lavandulyl-flavanone; 2,4,5,7-Tetrahydroxy-6-lavandulylflavanone; Sophoraflavanone G; SophoraflavanoneG; (-)-Vexibinol; norkurarinone; Kushenol F; vexibinol; Kushnol F; Kushenol



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

3 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Tsong-Hai Lee, Jiun-Liang Chen, Ming-Ming Tsai, Yi-Hsuan Wu, Hui-Ching Tseng, Li-Ching Cheng, Velayuthaprabhu Shanmugam, Hsi-Lung Hsieh. Protective Effects of Sophoraflavanone G by Inhibiting TNF-α-Induced MMP-9-Mediated Events in Brain Microvascular Endothelial Cells. International journal of molecular sciences. 2023 Dec; 25(1):. doi: 10.3390/ijms25010283. [PMID: 38203454]
  • Meng-Chun Wang, Wen-Chung Huang, Li-Chen Chen, Kuo-Wei Yeh, Chwan-Fwu Lin, Chian-Jiun Liou. Sophoraflavanone G from Sophora flavescens Ameliorates Allergic Airway Inflammation by Suppressing Th2 Response and Oxidative Stress in a Murine Asthma Model. International journal of molecular sciences. 2022 May; 23(11):. doi: 10.3390/ijms23116104. [PMID: 35682783]
  • Chung-Pu Wu, Yan-Qing Li, Tai-Ho Hung, Yu-Tzu Chang, Yang-Hui Huang, Yu-Shan Wu. Sophoraflavanone G Resensitizes ABCG2-Overexpressing Multidrug-Resistant Non-Small-Cell Lung Cancer Cells to Chemotherapeutic Drugs. Journal of natural products. 2021 09; 84(9):2544-2553. doi: 10.1021/acs.jnatprod.1c00584. [PMID: 34496204]
  • Zhong-Lin Sun, Shi-Chang Sun, Jian-Ming He, Jiang-Er Lan, Simon Gibbons, Qing Mu. Synergism of sophoraflavanone G with norfloxacin against effluxing antibiotic-resistant Staphylococcus aureus. International journal of antimicrobial agents. 2020 Sep; 56(3):106098. doi: 10.1016/j.ijantimicag.2020.106098. [PMID: 32707171]
  • Motahare Boozari, Saba Soltani, Mehrdad Iranshahi. Biologically active prenylated flavonoids from the genus Sophora and their structure-activity relationship-A review. Phytotherapy research : PTR. 2019 Mar; 33(3):546-560. doi: 10.1002/ptr.6265. [PMID: 30652369]
  • Alexandre Sze, David Olagnier, Samar Bel Hadj, Xiaoying Han, Xiao Hong Tian, Hong-Tao Xu, Long Yang, Qingwen Shi, Penghua Wang, Mark A Wainberg, Jian Hui Wu, Rongtuan Lin. Sophoraflavenone G Restricts Dengue and Zika Virus Infection via RNA Polymerase Interference. Viruses. 2017 10; 9(10):. doi: 10.3390/v9100287. [PMID: 28972551]
  • Fahimeh Moradi-Afrapoli, Samad Nejad Ebrahimi, Martin Smiesko, Matthias Hamburger. HPLC-Based Activity Profiling for GABAA Receptor Modulators in Extracts: Validation of an Approach Utilizing a Larval Zebrafish Locomotor Assay. Journal of natural products. 2017 05; 80(5):1548-1557. doi: 10.1021/acs.jnatprod.7b00081. [PMID: 28485933]
  • Zuo-Cheng Qiu, Xiao-Li Dong, Yi Dai, Gao-Keng Xiao, Xin-Luan Wang, Ka-Chun Wong, Man-Sau Wong, Xin-Sheng Yao. Discovery of a New Class of Cathepsin K Inhibitors in Rhizoma Drynariae as Potential Candidates for the Treatment of Osteoporosis. International journal of molecular sciences. 2016 Dec; 17(12):. doi: 10.3390/ijms17122116. [PMID: 27999266]
  • Hanqing Wang, Li Chen, Liming Zhang, Xiaojuan Gao, Yinghua Wang, Tao Weiwei. Protective effect of Sophoraflavanone G on streptozotocin (STZ)-induced inflammation in diabetic rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2016 Dec; 84(?):1617-1622. doi: 10.1016/j.biopha.2016.10.113. [PMID: 27832995]
  • Zhixin Yang, Wenjun Zhang, Xia Li, Baisong Shan, Jiajia Liu, Weizhe Deng. Determination of sophoraflavanone G and kurarinone in rat plasma by UHPLC-MS/MS and its application to a pharmacokinetic study. Journal of separation science. 2016 Nov; 39(22):4344-4353. doi: 10.1002/jssc.201600681. [PMID: 27808456]
  • Jaeyoung Kwon, Sunita Basnet, Jin Woo Lee, Eun-Kyoung Seo, Nanzad Tsevegsuren, Bang Yeon Hwang, Dongho Lee. Chemical constituents isolated from the Mongolian medicinal plant Sophora alopecuroides L. and their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages. Bioorganic & medicinal chemistry letters. 2015 Aug; 25(16):3314-8. doi: 10.1016/j.bmcl.2015.05.062. [PMID: 26073007]
  • Ping Chen, Xiuwen Zhang, Taomin Huang, Qianqian Yu, Nengneng Cheng. Metabolism of the hepatotoxic compound sophoraflavanone G in rat liver microsomes. Journal of food science. 2014 Jul; 79(7):T1462-8. doi: 10.1111/1750-3841.12501. [PMID: 24894298]
  • Qianqian Yu, Nengneng Cheng, Xiaojun Ni. Identifying 2 prenylflavanones as potential hepatotoxic compounds in the ethanol extract of Sophora flavescens. Journal of food science. 2013 Nov; 78(11):T1830-4. doi: 10.1111/1750-3841.12275. [PMID: 24245902]
  • Chi Zhang, Yue Ma, Hui-Min Gao, Xiao-Qian Liu, Liang-Mian Chen, Qi-Wei Zhang, Zhi-Min Wang, An-Ping Li. [Non-alkaloid components from Sophora flavescens]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2013 Oct; 38(20):3520-4. doi: . [PMID: 24490565]
  • Eui-Seok Chong, Gi Byoung Hwang, Chu Won Nho, Bo Mi Kwon, Jung Eun Lee, Sungchul Seo, Gwi-Nam Bae, Jae Hee Jung. Antimicrobial durability of air filters coated with airborne Sophora flavescens nanoparticles. The Science of the total environment. 2013 Feb; 444(?):110-4. doi: 10.1016/j.scitotenv.2012.11.075. [PMID: 23262327]
  • Ben Chung-Lap Chan, Hua Yu, Chun-Wai Wong, Sau-Lai Lui, Claude Jolivalt, Carine Ganem-Elbaz, Jean-Marc Paris, Barbara Morleo, Marc Litaudon, Clara Bik-San Lau, Margaret Ip, Kwok-Pui Fung, Ping-Chung Leung, Quan-Bin Han. Quick identification of kuraridin, a noncytotoxic anti-MRSA (methicillin-resistant Staphylococcus aureus) agent from Sophora flavescens using high-speed counter-current chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jan; 880(1):157-62. doi: 10.1016/j.jchromb.2011.11.039. [PMID: 22177235]
  • Jeong-Dan Cha, Sang-Eun Moon, Ji-Young Kim, Eun-Kyung Jung, Young-Soo Lee. Antibacterial activity of sophoraflavanone G isolated from the roots of Sophora flavescens against methicillin-resistant Staphylococcus aureus. Phytotherapy research : PTR. 2009 Sep; 23(9):1326-31. doi: 10.1002/ptr.2540. [PMID: 19288534]
  • Eun Mi Hwang, Young Bae Ryu, Hoi Young Kim, Dong-Gyu Kim, Seong-Geun Hong, Jin Hwan Lee, Marcus J Curtis-Long, Seong Hun Jeong, Jae-Yong Park, Ki Hun Park. BACE1 inhibitory effects of lavandulyl flavanones from Sophora flavescens. Bioorganic & medicinal chemistry. 2008 Jul; 16(14):6669-74. doi: 10.1016/j.bmc.2008.05.080. [PMID: 18565755]
  • Kanako Sasaki, Kouji Mito, Kazuaki Ohara, Hirobumi Yamamoto, Kazufumi Yazaki. Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens. Plant physiology. 2008 Mar; 146(3):1075-84. doi: 10.1104/pp.107.110544. [PMID: 18218974]
  • Seizo Sato, Jiro Takeo, Chihiro Aoyama, Hiroyuki Kawahara. Na+-glucose cotransporter (SGLT) inhibitory flavonoids from the roots of Sophora flavescens. Bioorganic & medicinal chemistry. 2007 May; 15(10):3445-9. doi: 10.1016/j.bmc.2007.03.011. [PMID: 17374486]
  • Jeong-Dan Cha, Mi-Ran Jeong, Seung-Il Jeong, Kyung-Yeol Lee. Antibacterial activity of sophoraflavanone G isolated from the roots of Sophora flavescens. Journal of microbiology and biotechnology. 2007 May; 17(5):858-64. doi: ". [PMID: 18051310]
  • Xiang-Lan Piao, Xiang Shu Piao, Sung Woo Kim, Jeong Hill Park, Hyun Young Kim, Shao-Qing Cai. Identification and characterization of antioxidants from Sophora flavescens. Biological & pharmaceutical bulletin. 2006 Sep; 29(9):1911-5. doi: 10.1248/bpb.29.1911. [PMID: 16946508]
  • Ping Zhao, Kenichiro Inoue, Isao Kouno, Hirobumi Yamamoto. Characterization of leachianone G 2"-dimethylallyltransferase, a novel prenyl side-chain elongation enzyme for the formation of the lavandulyl group of sophoraflavanone G in Sophora flavescens Ait. cell suspension cultures. Plant physiology. 2003 Nov; 133(3):1306-13. doi: 10.1104/pp.103.025213. [PMID: 14551337]
  • Hirobumi Yamamoto, Ping Zhao, Kenichiro Inoue. Origin of two isoprenoid units in a lavandulyl moiety of sophoraflavanone G from Sophora flavescens cultured cells. Phytochemistry. 2002 Jun; 60(3):263-7. doi: 10.1016/s0031-9422(02)00111-5. [PMID: 12031444]
  • H Yamamoto, A Yatou, K Inoue. 8-dimethylallylnaringenin 2'-hydroxylase, the crucial cytochrome P450 mono-oxygenase for lavandulylated flavanone formation in Sophora flavescens cultured cells. Phytochemistry. 2001 Nov; 58(5):671-6. doi: 10.1016/s0031-9422(01)00270-9. [PMID: 11672730]
  • T H Kang, S J Jeong, W G Ko, N Y Kim, B H Lee, M Inagaki, T Miyamoto, R Higuchi, Y C Kim. Cytotoxic lavandulyl flavanones from Sophora flavescens. Journal of natural products. 2000 May; 63(5):680-1. doi: 10.1021/np990567x. [PMID: 10843587]
  • H Tsuchiya, M Sato, M Iinuma, J Yokoyama, M Ohyama, T Tanaka, I Takase, I Namikawa. Inhibition of the growth of cariogenic bacteria in vitro by plant flavanones. Experientia. 1994 Sep; 50(9):846-9. doi: 10.1007/bf01956469. [PMID: 7925853]
  • J Yamahara, M Mochizuki, H Fujimura, Y Takaishi, M Yoshida, T Tomimatsu, Y Tamai. Antiulcer action of Sophora flavescens root and an active constituent. I. Journal of ethnopharmacology. 1990 May; 29(2):173-7. doi: 10.1016/0378-8741(90)90053-v. [PMID: 2374430]